Hydroxylamine → HCID 19017868, compound

Participants

Reaction Steps

To a solution of hydroxylamine (3.0 g, 20.9 mmol) from above, in THF (25 mL) was added trimethylsilylisocyanate (2.9 g, 25.2 mmol) and the reaction was stirred for 30 min. The reaction was treated with saturated aqueous NH4Cl and the aqueous mixture extracted with ethyl acetate (4×120 mL). The organics were combined, dried over MgSO4 then concentrated in vacuo. The resulting residue was chromatographed (silica gel, ethyl acetate:hexanes, 50:50) followed by crystallization in ethyl acetate/hexanes to afford N-hydroxy-N-1-(1-cycloheptyl)methylurea. m.p.=110°-112° C.; 1H NMR (300 MHz, DMSO-d6): δ1.09 (m, 2H), 1.2-1.7 (m, 10H), 1.79 (m, 1H), 3.14 (d, 2H, J=7.4), 6.16 (bs, 2H), 9.17 (s, 1H); Analysis calc'd for C9H18N2O2 : C, 58.04, H, 9.74, N, 15.04; Found: C, 57.85 , H, 9.60, N, 15.10.

Provenance & Evidence